This dissertation explores the production and maintenance of place reputation using three Chicago neighborhoods with different reputations: Wicker Park and reputational hipness, Bridgeport and reputational racism, and Woodlawn and reputational danger. Place reputation—a widespread, collective sense of what people think they know about a specific place based on the circulation of ideas, descriptions, accusations, and insinuations about that location—is consequential in the social lives of neighborhoods, particularly insofar as it impacts outsiders’ willingness to visit, spend money in, and otherwise interact with a neighborhood they do not intimately know. With this in mind, I examine the actions, strategies, and attitudes of neighborhood merchants. Using in-depth interviews and participant observation at targeted gatherings, I compare how these “frontline reputational actors”—a group both particularly attuned to their neighborhood’s reputation and motivated to impact it to their benefit—respond to their neighborhood’s reputation and its impact on their day-to-day decision-making and the long-term trajectory of their neighborhoods. In Wicker Park, actors with different economic incentives are able to coordinate action in pursuit of the consolidation of a financially remunerative reputation. In Bridgeport, one set of actors looks to reverse the neighborhood’s exclusionary reputation—which they object to morally and suffer from financially— but in pursuing this strategy of “undefending” the neighborhood, create a new moral order that is itself potentially exclusionary. In Woodlawn, merchants bemoan a reputation that drives away customers, but face obstacles to change it since a different actor in the neighborhood has been able to obtain financial resources and political power not in spite of the neighborhood’s reputation for danger, but because of it. These processes all rely on the use of neighborhood reputation as socially meaningful heuristics that motivate action, among both customers and merchants. Additionally, each process is embedded not in a single neighborhood, but a constellation of them, with the reputation of one place co-constituted with the reputations of other places across space and time. The dissertation concludes by considering the practical consequences of place reputation for neighborhood outcomes as well as examining how place reputation might be productively studied at different scales.